Evidence suggests that Second Life (SL) is well received by those studying at a distance; however, little has been done to evaluate how a structured orientation session may affect students' use and perception of SL. Consequently, this study explored orientation timing and its effect on a group of students registered in a part-time distance education master's degree program at a large UK University open to international students. An online survey was designed and administered to assess students' use and perception of SL use and whether these variables changed based on the timing of orientation to SL and its subsequent use. A series of Likert-type scale items were organized to gather the following information: student demographics; and students' experience with, and thoughts of, SL. Results indicated that the use of an orientation session close to subsequent use of SL for learning activities did positively affect students' use and perception of SL. Consequently, recommendations from the current findings suggest that if educators foresee a pedagogical benefit to using SL then it is important to ensure that students are provided with a timely and structured orientation to prior to its utilization.